Why won't my purchased music play?

It went like this:
My sister recommended a song for me to look up, so I did. I liked it and I bought/downloaded it.
After sampling the rest of the songs on the album, I decided to buy the whole thing. I noticed that the price of the album hadn't changed after I paid for the first song (like it usually does), but the difference was 99 cents so I didn't care enough to press the issue. Apple support is nightmare to get ahold of, and my time's worth more than 99 cents.
Anyway, I paid full price for the album and the songs definitely downloaded (including the one song I'd already downloaded, which re-dowloaded).
I synced my iPhone 4s and everything looked well enough.
The music plays on my Macbook Pro just fine.
But when I try to listen to the new music on my phone, the first 3 or 4 songs refuse to play (inlcuding the first song I paid for, and has been downloaded twice.)
Why?
I deleted the music off my itunes and redownloaded them from the cloud, re-synced, and still the same problem.
Why?

I deleted the music from my itunes, synced the phone (without transferring purchases), redownloaded the music, then resynced with the newly redownloaded music. Still nothing.
Do you mean resetting as in factory resetting the phone? No, I haven't done that. I was hoping the problem was with the mp3, not my phone or phone's operating system. But I can't seem to find a easy way to ask apple. iTunes' help/support just links me here. If i could email them and ask, that'd be nice. But I don't know how to even do that. Their website is a labyrinth.

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Why won't my purchased music transfer into my songs/albums folders?

I'm using the new format for ITunes for the first time, and have run into an issue. When I purchase songs, they go to my "Playlists" Folder, but when I click on my "songs/albums" folders I just see the picture of the laptop with the options to "Scan for Music" which does nothing, or go to ITunes Store, which does as it says.
The new layout is a bit confusing to me, but I have tried manually adding a file to my library which doesnt add them, and also going from my Purchased Playlist then clicking "Add To" it will bring up my Songs Folder and I can either select the songs and click Done, or not and click done...the songs folder slides away and nothing at all is transferred.
I'm a bit confused, why doesnt it simply add them to your normal library as before in addition to "purchased"? Beyond that, what am I missing in getting them into my library?

And if none of those work, you may want to try this test:
1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.
If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.
The following articles will help you.
Authorization and Deauthorization.
How to create a new user account in Windows.
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How to recreate your iTunes library.

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Hi bsiria,
If you are having an issue with one or more songs not playing completely, you may want to troubleshoot this by using the steps in this arcticle -
Songs in iTunes may not play back completely
http://support.apple.com/kb/TS4357
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If iTunes in the Cloud is available in your country, try the following steps to resolve the issue:
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Click on the Purchased link in the iTunes Store to view your previously purchased music.
Download your previously purchased song from this list.
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http://support.apple.com/kb/HT2519
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Why won't my purchased music play?

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